Lethal effect of thiophene and phenol rich leaf extract from Ferula asafoetida on Dacus ciliatus (Loew)

doi:10.21203/rs.3.rs-3602057/v1

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Lethal effect of thiophene and phenol rich leaf extract from Ferula asafoetida on Dacus ciliatus (Loew)

https://doi.org/10.21203/rs.3.rs-3602057/v1

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Studies were conducted to evaluate the toxicity of methanol (MeOH) extract from Ferula asafoetida Linn. (Umbelliferae) leaves on female adults and larvae of the lesser pumpkin fly, Dacus ciliatus (Diptera: Tephritidae). Direct-dip bioassays for larvae and topical bioassays for adults of fly were used to assess mortalities. Mortality increased significantly with rising concentrations. The intermediate lethal concentrations (LC₅₀), calculated 7.3 mg/ml (7300 ppm) for larvae. The female adult LC₅₀ was 409 µg/insect. The chemical composition of the isolated MeOH extract from Ferula asafoetida leaves was examined by gas chromatography-mass spectrometry. The major compounds were 2, 3, 4, 5-Tetramethyl thiophene (22.1%), Phenol, 3-pentadecyl- (21.2%) and Mono (2-ethylhexyl) phthalate (15.98%). The results suggested that the extract from the tested plant could be used as a potential control agent for this pest.

Bioassay

Chemical composition

Dacus ciliatus

Extract

Insecticide

Dacus ciliatus Loew (Dip.: Tephritidae) is an important agricultural pest worldwide that mainly attacks cucurbit crops. In many areas such as Africa, Atlantic Islands, and oriental Asia, this fly is responsible for high infestation rates in cucurbit crops and induces important damages (White and Elson–Harris 1992). Pumpkin flies usually lay their eggs in the young fruit; Larvae eat surface, which renders it unsuitable for marketing. The published reviews, such as the one by White and Elson-Harris (1992), are frequent and provide a simple background to suggest integrated pest management methods for this pest. In addition, most of the knowledge is based on laboratory studies or field experiments using either male pheromone or food–baited traps or collecting of infected fruits (Dhillon et al. 2005).

Today, there is increasing interest in the use of natural products from plants to control pests. Secondary metabolites consist of compounds the concentration of which may be only few percent or less of the dry weight. The function or importance of these compounds to plant development is not always clear, although many of them are involved in defense mechanisms or act as signaling substances in plants (Luckner 1990).

Limited natural products have reached the marketplace, partially because their efficiency is still lower than that of presently used synthetic compounds. However, there is a new attention in plant products as sources of novel insect controlling agents, because they may be decomposable to harmless compounds, thus reducing the accumulation of adverse residues, leading them to be more ecologically friendly compared to synthetic mixtures. The search for environmentally safe pesticides has fostered research on the use of plant materials for the protection of crops against pests, both on the field and in storage. Secondary plant metabolites are a large reservoir of chemicals with biological activities. Phytochemicals such as rotenone, nicotine and pyrethrin were all used as pesticides before the advent of synthetic insecticides. Numerous species of Myrtaceae, Asteraceae, Piperaceae, Meliaceae and Annonaceae families are known to have different chemical compounds which act as antifeedants, repellents or development inhibitors to many insect pest species (Srivastava et al. 2001).

Ferula assafoetida is a monecious, herbaceous, constant plant. It is giant plant 2–3 m high, with a circular mass of 30–40 cm. Leaves are compound, 2–4 pinnate very huge and bipinnate, pubic. It is native to central Asia, eastern Iran to Afghanistan.

The chemistry of Ferula genus has been studied by many and is well documented as a good source of biologically active compounds such as sesquiterpene derivatives (Kogure et al. 2004; Motai et al. 2004) and sulfur containing compounds (Iranshahi et al. 2008).

Literature on biological activity and insecticide evaluation on F. asafoetida essential oil were reported in various studies (Sonigra and Meena 2021; Estekhdami et al. 2020; Bahrami et al. 2016; Koorki et al. 2022).

Essential oil characterized by readily evaporation when exposed to air at normal room temperature. Their toxicities, arresting and repellent effects to stored-product insects and greenhouse pests have been of special interest. Although some commercial products based on repellent odours have been developed recently (for example, Isman 2000), owing to the high volatility of some plant essential oils, their application in open fields may not control insect pests satisfyingly. So, MeOH extract from Ferula asafoetida leaves studied in this research. On the other hand, to our knowledge, there is no literature referring to the use of Ferula assafoetida extract against Dacus ciliatus.

The objective of the present study was to determine chemical composition and its insecticidal potential of MeOH extract from Ferula asafoetida leaves against the lesser pumpkin fly, Dacus ciliatus (Dip.: Tephritidae).

Plants and Solvent Extraction

Aerial parts (foliage) of F. assafoetida were collected from Takhteh-ye Jan villages, located in Darmian County, South Khorasan Province, Iran (33° 13' 32" N, 59° 59' 39" E, 1900 m a.s.l.). The plant materials were dried naturally on laboratory benches at room temperature (23–27°C) until crisp.

For the extraction of secondary metabolites, the leaves of F. assafoetida were dried under shade and then powdered with a mechanical grinder. The powder was fermented with MeOH alcohol 95% (ratio 1:4 w/v), the containers were covered with Para film and the mixture was shaken (300 rpm) for 24 h to ensure proper soaking of the plant product. After the completion of extraction, the liquid extract was filtered through Whatman No.1 filter paper fitted in a Buchner funnel using suction. The extracted plant substances were kept in container cover with aluminum foils at 4°C.

To determine the dry weight of pure extract at one milliliter of solution, the small parts of solution (5 ml) were collected in three replicate, separately and allowed to dry completely at 60°C in oven. The methanol extraction of leaves of F. asafoetida gave a crude extract in 1.5% (w/v) density.

Larvae Bioassay

Larval-dip bioassays were conducted to determine the contact toxicity of the MeOH extract of F. assafoetida on Dacus ciliatus larvae. On the basis of preliminary testes, six concentrations of MeOH extract were used in the test. The randomly selected last instars larvae were separately immersed in a prepared concentration of extract solution for 3 s as described by Watkinson et al. (1984). To absorb excess moisture, the treated larvae placed on paper towel and then ten randomly selected larvae transferred to a plastic petri dish (9cm diameter), the bottom of which was lined with a filter paper (Whatman no. 1, 9 cm) and held at 25±1 °C. Control larvae were dipped in MeOH for the same period of time.

The treatments were replicated four times with ten larvae per each treatment, and larval mortality was recorded 24 h after treatment. Larvae were considered dead if they did not move when lightly prodded with forceps.

Adult Bioassay

A direct contact bioassay was conducted to compare the response of newly emerged (aged two days) adult cucurbit fly. For bioassay test, various volumes of the MeOH extracts of Ferula asafoetida leaves (250–3000 µl) were completely dried at room temperature under mild fanning and the residue was weighted and re-dissolved in the 0.5 ml water as solvent.

The bioassays were carried out by topical application of a 10µl (5 µl droplet in two stages with 10 minutes interval times) of each concentration of the MeOH extract (in distilled water) to the thorax of chilled (5°C for 5 min), anaesthetized female flies (1- to 2-day-old adults) by using a an Eppendorf micropipette (0.5–10.0 µl, Brinkmann Instruments, Westbury, NY). Total of 25 flies were treated for each concentration of extract with five replicates for each treatment. The treated flies were transferred to the breeding room (25 ± 2°C) and were kept in a 120 ml net-coated plastic cup (5 adults / cup), the bottom of which was lined with a filter paper, and fed with fifty percent honey solution. Control insects were treated with methanol dried and water re-dissolved, alone. Mortality was observed 24 h after exposure and LC₅₀ (median lethal dosage) was calculated. No mortality was recorded in the controls.

Gas chromatography–mass spectroscopy of extract

The MeOH extract was analyzed on a gas chromatograph mass spectrometer (GC-mass) (Shimadzu-17A-QP5050, Japan). The GC column was DB-5 (30 m × 0.25 mm i. d, 0.25 µm film thickness). The column oven temperature was set at 60°C for 3 min, and then increased to 260°C at a rate of 5°C/min. Injector and detector temperatures were 230 and 245°C, respectively. The GC mass analysis was carried out with the same characteristics as used in GC. The ionization energy was 70 ev with a scan time of 1s and mass range of 40–500 amu. Unknown essential oil was identified by comparing its GC retention time to that of known compounds and by comparison of its mass spectra, either with known compounds or published spectra.

Statistical analysis

Mortality data from bioassays were analyzed using probit analysis and analysis of variance (ANOVA) with SPSS₂₄. LC₅₀ values were considered significantly different if 95% confidence limit did not overlap.

Contact Toxicity

Probit analysis of the concentration-mortality response of Dacus ciliatus indicated that the larvae and adults were susceptible to F. assafoetida extract. There were significant differences between tested concentrations after 24 h. The mortality increased significantly with rising concentrations (Fig. 1, 2) (F_5,23= 34.07; P>0.001 for larvae and F_6,34= 22.43; P>0.001 for adults).

Table 1 shows the parameters of probit regression line of Dacus ciliatus adults and larval susceptibility to MeOH extract of F. asafoetida at different concentration.

After examination of different concentration on last instar larvae, crude extract in concentration of 21 mg/ml showed 95% mortality. By testing other concentration, LC₅₀ calculated 7.3 mg/ml (7300 ppm) for larvae. Concentration of 900 µg/female showed 84% mortality in tested adults. The adult LC₅₀ was determined 409 µg /female (Fig. 2).

Chemical composition of MeOH extract

The chemical composition of the MeOH extract from F. asafoetida leaves is presented in Table 2 The major compounds were 2, 3, 4, 5-Tetramethyl thiophene (22.09%), Phenol, 3-pentadecyl- (21.18%), Mono (2-ethylhexyl) phthalate (15.98%), 2, 3, 4, 5, 6, 7, 9,10-octamethyl- syntricyclo [4.2.2.0(2, 5)] deca-3, 7, 9-triene-1, 8- dicarboxyanhydryde (5.79%), Phytol (5.18%), Sulfonium, dimethyl (5.02%), Octadecatrienoic acid methyl ester (4.33%), Neophytadiene (3.93%), Benzylcarbamate (2.65%), 1-Deuteronaphthalene (2.09%) and Photonerol B (2.04%) in the MeOH extract from F. asafoetida leaves.

Due to the development of insecticide resistance and risks to human health and the environment of synthetic compounds, the search for alternative pesticides is encouraged. The use of plant essential oils and extract in insect pest control is a suitable alternative method for reduction of the side effects of chemical pesticides on the environment (George et al. 2014).

The secondary compounds of plants make up a vast repository of compounds with a wide range of biological activities. In the present study, the plant extract exhibited good insecticidal properties. According to the results, insecticidal activity of the extract of F. asafoetida showed that the MeOH extract with LC₅₀ = 7.3 mg / ml for larvae and LC₅₀ equal to 409 µg /female for adults had high toxicity effect.

Based on our knowledge, although, there are some literatures on cytotoxic, pesticide and insecticidal activity of F. asafoetida, no study has been reported concerning the toxicity of Ferula assafoetida extract against Dacus ciliatus. It has been reported that dried root latex powder of F. assafoetida is an important source of botanical molluscicides which possess time- and concentration dependent toxicity (Kumar and Singh 2006) and this toxicity seems to be mainly due to the water-soluble components, particularly ferulic acid and umbelliferone (Saleem et al. 2001; Hirotaka et al. 2003). The methanol extracts of oleo-gum-resin of F. assafoetida exhibited dose-dependent cytotoxic effect on Artemia salina larvae, a simple zoological organism (marine invertebrate), with LC₅₀ value of 28 µg/mL (Bagheri et al. 2010).

Ferula species essential oil has been described by other research groups as insecticidal and some of its active derivatives were identified. Lethal concentrations (LC₅₀) of the essential oil of F. assa-foetida were examined after 12 (9.04 µL/L air) and 24 (4.64 µL/L air) hours whereas at a 10 µL/ml concentration the essential oil showed repellent activity against Aphis gossypii Glover (Koorki et al. 2022).

In other research, the poisonous effects of the essential oil obtained from the oleo-gum-resin of F. assafoetida was studied on two species of stored-product pests, larger grain borer, Prostephanus truncatus (Coleoptera: Bostrichidae) and Trogoderma granarium Everts (Coleoptera: Dermestidae), an agricultural insect pest, cotton leaf worm, Spodoptera littoralis Boisduval (Lepidoptera: Noctuidae), and two public health relevance, Culex quinquefasciatus Say (Diptera: Culicidae) and Musca domestica Linnaeus (Diptera: Muscidae), and according to the results, the essential oil were active against important insect pests and vectors (Pavela et al. 2020).

Effects of Ferula assa-foetida L. ethanolic extracts on lethality and some physiological features of Mediterranean flour moth, Ephestia kuehniella Zeller (Lepidoptera: Pyralidae) larvae, were studied and the results showed that the F. assa-foetida extract considerably reduced the activity of chymotrypsin, β-glucosidase, lipase and trypsin enzymes compared to the control insects (Ajamhassani, 2021).

Analyzing the MeOH extract from F. asafoetida leaves by GC/MS showing that twenty compounds representing 97% of the total detected compounds, in which 2, 3, 4, 5-Tetramethyl thiophene (22.09%), Phenol, 3-pentadecyl- (21.18%), Mono (2-ethylhexyl) phthalate (15.98%) were reported as the chief compounds. The present result was similar to the other literature reported earlier. The most distinctive feature that can be applied for the classification of Ferula genus is the presence of sulfur containing compounds. In common, sec-butyl part of sulphur-containing compounds is considered as the chemotaxonomic indicator of the family Apiaceae. sec-Butyl derivatives of sulphur containing compounds have formerly been reported from Ferula species including F. assa-foetida (Iranshahy and Iranshahi 2011).

Relative richness of sulfur-containing compounds in the seed and oleogum resin essential oil of F. assafoetida were 50 and 80 percent, respectively (Sahebkar and Iranshahi 2010). A sulfur-containing hydrocarbon (E)-sec-butyl propenyl disulfide, was the chief element (62.7%) in the essential oil of this plant (Kavoosi et al. 2013).

Some studies showed that F. assafoetida possesses a highly strong, persistent and nasty alliaceous aroma. The main constituents of its essential oil which cause its odor are sulfur compounds. The study of chemical profiles of nine samples revealed that (E)-propenyl sec-butyl disulfide (37–54%) was the abundant compound with (Z)-propenyl sec-butyl disulfide (12–23%) in the essential oils (Hassanabadi et al. 2019). Also, (E)-sec-butyl propenyl disulfide (Z) and (E)-β-ocimene, β and α-pinene were the major chemical components of Ferula assa-foetida (Koorki et al. 2018).

Similar to our results, sulfur-containing metabolites such as 2,5-diethylthiophene, trimethylthiophene and phenol 2-methyl-5-(1-methylethyl) was found in the essential oil of Ferula assafoetida (Kavoosi and Purfard 2013) and diethyl phthalate (13.09%) was observed in essential oil of Ferula galbaniflua Boiss. & Buhse (Andrade et al. 2016). Also, 2-isopropyl-5-methylphenol were recognized as primary chemical constituents in methanolic extracts and essential oil of Ferula microcolea (Boiss.) (Amiri 2014)

The results showed the presence of bioactive compounds in the MeOH extract from F. asafoetida leaves extracts. The toxicity of the extract could be caused by the bioactive compounds present in the extract. Some of these compounds and their derivatives have been previously reported for their insecticidal properties against other insect pests.

Existence of the sulphur-containing compounds in MeOH extract of Ferula assa-foetida leaves, are of pharmacological interest because they could have insecticidal effect and so contribute to the plant's overall defense mechanism (Breteler and Ketel 1993; Huang et al. 2000; Nwachukwu et al. 2012). Sefidkon et al. (1998) showing that essential oil, (E)-1-propenyl sec-butyl disulfide is the major component (58.9%) in Iranian Ferula assafoetida. Also, polysulfides were found in the volatile oil. It has been concluded that these compounds might be responsible for the oil desirable properties such as insecticidal activity (Huang et al. 2000).

The thiophene derivatives symbolize one of the most thoroughly examined groups of phototoxic phytochemicals (Downum 1992; Breteler and Ketel 1993). The sulfur containing compounds such as thiophenes detected from Tagetes owning high insecticidal (Perich et al. 1995) and nematocidal activity (Breteler and Ketel 1993; Kyo et al. 1990). Three new insecticidal thiophene derivatives, xanthopappins A-C, were isolated from Xanthopappus subacaulis, that exhibited significant photoactivated insecticidal action against the fourth-instar larvae of the Asian tiger mosquito, Aedes albopictus Skuse (Diptera: Culicidae) (Tian et al. 2006).

The effect of phenolic compounds on larvae of the mosquito, Stegomyia aegypti (= Aedes aegypti), the vector of dengue, has been also reported (Marston et al. 1993; Chowdhury 2008). Aluminium chloride obtained from alder leaf, known for its phenolic complexing activity, is reported to have the larvicidal activity against Stegomyia aegypti (David et al. 2000).

This study suggests that F. assafoetida leaf extract may be a potential protectant due to its contact toxicity activity against Dacus ciliatus. The results of this study highlight the potential benefit of further research into suitable formulations, as well as cheaper and more potent synthetic analogs.

In conclusion, the results obtained in this study clearly indicate that F. assafoetida has a sufficient potential for use as a source for management and control of insect pests. However, the exact mechanism of this effect remains to be clarified and further investigations including chronic toxicity studies and activity-guided fractionation must be performed in order to assess the real toxicological profile and the active compounds of the extract.

Conflict of interest

The authors declare that they have no conflict of interest.

Acknowledgment

This study is a part of MSC program in the University of Zabol, Iran. The corresponding author gratefully acknowledges the financial support from the University of Zabol (Grant No 0084).

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Table 1. Efficiency of methanol extract from Ferula asafoetida leaves against Dacus ciliatus larvae and female adults.

Insect stage	No.	c²	Probability	Slope ± SE	Lc₅₀	95% Confidence Interval
Insect stage	No.	c²	Probability	Slope ± SE	Lc₅₀	Lower limits	Upper limits
Larvae	280	3.97 (4)	0.41	2.58±0.37	7.29	6.10		8.51
Adults	175	0.76 (4)	0.94	2.57±0.45	408.9	335.3		510.0

Ten individuals per replicate, four replicates per concentration, six concentrations per assay for larvae. Five individuals per replicate, five replicates per concentration, six concentrations per assay for adults.

Lc: lethal concentration (mg/ml solvent for larvae and µg/insect for female adults)

Table 2. Chemical composition of methanol extract from Ferula asafoetida leaves

Compounds	Concentration (%)		Retention time (min.)
Chlorophenylacetic acid	0.77		3.82
2,3,4,5-Tetramethyl thiophene	22.09		4.34
1-Deuteronaphthalene	2.09		6.26
(+)-5,6-dehydrocamphor	0.45		11.23
2-propyldecan-1-ol	0.97		12.08
Di-isodecyl phthalate	0.38		13.50
Sulfonium, dimethyl	5.02		14.90
Photonerol B	2.04		15.50
Neophytadiene	3.93		19.54
Citronellyl propionate	0.61		20.43
Octadecatrienoic acid, methyl ester	4.33		21.13
Phytol	5.18		24.80
2-chloro-1,3-dimethyl-1,3,- diazaphosphacyclopentane	0.41		25.01
3,3,4,4-Tetramethyl-2-pentanone	1.35		26.10
Phenol, 3-pentadecyl-	21.18		26.92
2,3,4,5,6,7,9,10-octamethyl-Syntricyclo[4.2.2.0(2,5)]deca-3,7,9-triene-1,8-Dicarboxyanhydryde	5.79		27.45
Phenol, 3-methyl-	0.96		29.55
Benzylcarbamate	2.65		29.74
1-(2-Hydroxyethoxy) tridecane	0.76		29.85
Mono(2-ethylhexyl) phthalate	15.98		29.95
Other compounds		3.05

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Lethal effect of thiophene and phenol rich leaf extract from Ferula asafoetida on Dacus ciliatus (Loew)

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Abstract

Figures

Introduction

Materials and methods

Plants and Solvent Extraction

Larvae Bioassay

Adult Bioassay

Gas chromatography–mass spectroscopy of extract

Statistical analysis

Results

Discussion

Conclusion

Declarations

Conflict of interest

Acknowledgment

References

Tables

Status:

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